2,3-dimethyl-2H-indazol-6-amine hydrochloride Chemical Properties

Melting point:

>230°C (dec.)

storage temp. 

Inert atmosphere,Room Temperature

solubility 

DMSO (Slightly), Methanol (Slightly)

form 

Solid

color 

Pale Beige to Light Beige

Stability:

Hygroscopic

InChI

InChI=1S/C9H11N3.ClH/c1-6-8-4-3-7(10)5-9(8)11-12(6)2;/h3-5H,10H2,1-2H3;1H

InChIKey

DYTQJZDNKWQSLS-UHFFFAOYSA-N

SMILES

N1=C2C(C=CC(N)=C2)=C(C)N1C.[H]Cl

2,3-dimethyl-2H-indazol-6-amine hydrochloride Usage And Synthesis

Description

2,3-dimethyl-2H-indazol-6-amine hydrochloride is a pharmaceutical intermediate impurity, a by-product from the preparation of pazopanib hydrochloride, which can be used as an impurity standard solution for experimental analysis.

Chemical Properties

Powder

Uses

2,3-Dimethyl-6-amino-2H-indazole is an impurity in the synthesis of Pazopanib (P210925) hydrochloride, an oral angiogenesis inhibitor targeting VEGFR and PDGFR.

Synthesis

General procedure for the synthesis of 2,3-dimethyl-6-amino-2H-indazole hydrochloride from 2,3-dimethyl-6-nitroindazole: 2,3-dimethyl-6-nitro-2H-indazole (1.13 g) was dissolved in 2-methoxyethyl ether (12 mL) under stirring at 0°C, and then 4.48 g of stannous chloride in 8.9 mL of concentrated hydrochloric acid was added drop by drop over a period of 5 minutes solution. After the dropwise addition was completed, the ice bath was removed and the reaction mixture continued to be stirred for 30 minutes. Subsequently, about 40 mL of diethyl ether was added to the reaction solution to induce precipitation of the product. The precipitate was separated by filtration and washed with diethyl ether to afford the yellow solid product 2,3-dimethyl-6-amino-2H-indazole hydrochloride (1.1 g, 95% yield). The structure of the product was confirmed by 1H NMR (300 MHz, DMSO-d6) and mass spectrometry (ES+): 1H NMR δ 7.77 (d, J=8.9Hz, 1H), 7.18 (s, 1H), 7.88 (m, 1H), 4.04 (s, 3H), 2.61 (s, 3H); MS (ES+, m/z) 162 (M+H).

References

[1] Patent: WO2003/106416, 2003, A2. Location in patent: Page 42-43
[2] Patent: WO2007/64753, 2007, A2. Location in patent: Page/Page column 27
[3] Journal of Medicinal Chemistry, 2008, vol. 51, # 15, p. 4632 - 4640
[4] Patent: WO2006/20564, 2006, A1. Location in patent: Page/Page column 14
[5] Patent: EP2311825, 2015, B1. Location in patent: Paragraph 0178 - 0180

2,3-dimethyl-2H-indazol-6-amine hydrochloride(635702-60-2)Related Product Information

• 2,3-DIMETHYL-2H-INDAZOL-6-AMINE
• N-(2-chloropyriMidin-4-yl)-N,2,3-triMethyl-2H-indazol-6-aMine
• Pazopanib Related Compound 3
• 2(1H)-Pyrimidinone, 4-chloro- (6CI,9CI)
• 1,3-Dimethyl-6-nitro-1H-indazole
• Pazopanib Related Compound 2
• 3-Methyl-6-nitro-2H-indazole
• Pazopanib
• 2,3-DIMETHYL-6-NITRO-2H-INDAZOLE
• Pazopanib Hydrochloride
• 2-Ethyl-5-nitrobenzenamine ,98%
• Pazopanib Impurity 9
• N-(2-Chloropyrimidin-4-YL)-2,3-dimethyl-2H-indazol-6-amine
• Pazopanib Impurity 10
• 1,3-DiMethyl-6-aMino-1H-indazole
• Pazopanib Impurity 2
• 2-Methyl-5-nitrobenzenesulfonamide
• 3-AMINO-4-METHYLBENZENESULFONAMIDE